Derek Sivers

By Derek Sivers

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Category: Self-Improvement

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Rob Simpson
 Nov 2, 2019
Great podcast. I subscribe to many longform ones. Nice to have some quick listens. As usual with Derek, short but pack a punch!


Episode Date
And if only 1% of those people…

A musician had manufactured 10,000 copies of his CD in anticipation of 10,000 orders that were sure to come through that week.

He had bought a quarter-page advertisement in the back of a magazine with a circulation of one million people.

He kept saying, “If only one percent of the people reading this magazine buy my CD, that’ll be 10,000 copies! And that’s only one percent!”

He bought 10,000 padded mailers and mailing labels. He converted his garage into a big mailing center.

He kept saying, “Maybe we can get like 10 percent! That’s 100,000! But worst case scenario — if only 1 percent — that’s still 10,000!”

The magazine issue came out, and... nothing. He bought an issue. There was his ad. But the orders were not coming in! Was something wrong? No. He tested it. Everything was working.

Over the next few weeks he received four orders. Total CDs sold: 4.

He forgot there was a number lower than one percent.

I think of this every time I hear business plans that say, “With over one billion iPhones sold, our app is sure to…”

Nov 18, 2019
How I became Ryuichi Sakamoto’s guitarist

In 1991 I was 22 years old, and had moved to New York City to be a professional musician. I had a little home studio, and was doing some random gigs around town.

My roommate, Hoover Li, was an assistant engineer at a huge recording studio in midtown. Ryuichi Sakamoto was there recording his new album “Heartbeat”.

Ryuichi mentioned to Hoover that he was looking for a guitarist for his next tour of Japan. Manu Katché on drums and Victor Bailey on bass. But no guitarist chosen yet.

Hoover said, “My roommate is a great guitarist.”

Ryuichi said, “But what does he look like?”

Hoover came home around midnight, and told me the big news. I was already a fan, since I loved his album “Beauty”, and thought this would be a dream gig.

Hoover gave me a tape of the new (unreleased) Heartbeat album, but told me he needed it back in the morning.

I listened to the whole album carefully. There was no guitar on it. I was already imagining parts. I started playing along with it.

I stayed up all night writing guitar parts for his album, recording them in my home studio, then mixing together his album — now with my guitar — back into a new master.

In the morning, as Hoover was waking up to go into the studio, I gave him his tape back, but also a 2nd tape of the whole album, now with my guitar, for him to give to Ryuichi.

I only slept a few hours, but woke up with the feeling like that wasn’t enough. I had to do more to prove I really wanted this gig.

I bought six of his older CDs, and listened to them all day. One had a particularly hard cello part in the middle. I decided to transcribe it and write out the transcription in perfect bass-clef notation in pencil on staff paper, just to show him I could read and write music. Again, I asked Hoover to deliver it to Ryuichi, telling him I really wanted this gig.

The next day I got a call from his manager, giving me the dates, asking if I was available! A month in Japan. Two weeks of rehearsal in Tokyo, then two weeks touring the country.

I said yes, but the manager said they were undecided, and would get back to me. (Oh no! Are they changing their mind?)

Hoover said Ryuichi wanted me to come down to the studio to meet him. I did. We barely spoke. He’s very quiet. But at one point I said, “Your manager said they’re undecided,” and Ryuichi just smiled and said, “I decide. Not them. I’ve decided. Don’t worry.”

Whoo-hoo! Got the gig!

When we were rehearsing in Tokyo, all the other band members were given very specific charts, but Ryuichi would say to me, “Just do what you did before.”

Dream gig. 22 years old. In Japan. Playing to the famous 10,000 seat Tokyo Budokan concert hall, and more. Awesome.

I did OK, but as the youngest, I was definitely the punching bag of the other band members. It was rough.

Later that year, we got hired back to play the World Expo in Seville, Spain, this time with Darryl Jones on bass.

I made the fatal mistake of thinking they were providing the outfits for us, like they had done in Japan. So just 30 minutes before showtime, (televised and all), I’m in shorts and a t-shirt, asking where everyone else got their nice outfits, and found out we were supposed to bring back the ones they gave us in Japan. Ooops! They tossed some other clothes on me, but were gravely disappointed, and I never heard from them again. (I’ll never know if it was because of the clothes or my playing.)

Oh except a year later, I was living on the Oregon Coast, and got a little happy birthday postcard from Ryuichi himself.

My personal lessons learned from this story:

  • Being in the middle of things increases your chances for opportunities.
  • Everything great that happens in your career starts with someone you know.
  • When you hear of an opportunity you want, you have to go for it completely, over-the-top, not casual, and work your ass off to get it.
  • The tiniest detail can derail everything.
Ryuichi Sakamoto’s band — 1992

In this picture, from left to right, is translator Mei Fang, Everton Nelson, Satoshi Tomiie, Vivian Sessoms, Victor Bailey, Manu Katché, and me at the bottom.

Nov 17, 2019
Sammy Cahn said thank you

In 1990, at the age of 20, I moved to New York City and got a job as the tape room guy for Warner/Chappell Music Publishing.

It was a small office, about 12 people, but the door to one room was always closed. I assumed it was unused.

One day, after a few months, I hear an old man yelling, “Goddamn it! What’s wrong with this typewriter? Can’t someone make a simple goddamn typewriter work?! What the hell?”

He was in the previously-closed room, door open, fighting with the typewriter. I went in to help, and as I was fixing it, I noticed some press clippings on the wall about Sammy Cahn, then looked at the man and realized it was Sammy Cahn!

Legendary songwriter Sammy Cahn who wrote most of those huge Frank Sinatra hits! “Love and Marriage”, “Let It Snow, Let It Snow, Let It Snow”, “All the Way”, “High Hopes”, “Call Me Irresponsible” and many more. He lived in Los Angeles, but they kept a New York office for him, which he’d visit every few months.

I fixed his typewriter, then said, “Sammy — my name’s Derek. If you ever need anything, just buzz number 12 on your phone and I’ll be glad to help.” He scowled at me, then waved me out of his room.

But from them on, every time he’d come into town, I’d be the first to know, because his voice would bark over my intercom, “[beeeep] Derek, goddamn it, get in here!” Everyone else at the office avoided him.

One day, he had me go to the Time/Warner Cafeteria to get him his favorite bowl of soup. When I gave it to him, he yelled at me for not filling the cup all the way to the top.

One day, he had me get some Ben Gay from the drug store. When I gave it to him, he asked me to rub it on his neck, which I did, but I used too much, and he yelled at me for making his neck all goopy.

But I liked him. His cranky personality was like a running joke, and didn’t bother me a bit.

He was still writing songs every day. Usually custom lyrics for existing songs, tailored for friends’ birthdays or special events. But he was still writing new songs, too.

I spent hours with him helping him autograph his songbooks. He patiently answered all of my eager questions about songwriting. (“As soon as I hear a melody, I can tell you what that song will be called. The piece of paper goes in the typewriter, I start typing, and when it comes out, it’s done! No edits!”)

I’d find an excuse to be in the room when he was writing new songs with composers like Walter Afanasieff. I played him some of my songs, and he gave me advice. I was thrilled. 20 years old, living in New York City, and working with Sammy Cahn.

One day as I was doing something in the kitchen, he was yelling at the coffee machine. (“What’s wrong with the goddamn coffee? Can’t I get a simple goddamn cup of coffee anymore? What are all these buttons?”)

I laughed and said, “Sammy, you know what? I like you.”

He looked at me, and his usually-scowling face went blank. Like the mask he always wears had dropped. Like he hadn’t heard “I like you” in a long long time.

He paused for a while, then said, in an unusually nice voice, “Thank you. You’re a very nice man.”

Then he went back to yelling at the coffee machine.

A few months later, in November 1992, I quit my job to be a full time musician, and went out to an isolated part of the Oregon coast to record. No TV, no newspaper, no internet, no radio. Just me, all alone, just recording. Warner/Chappell Music was long behind me, and I didn’t keep in touch with anyone.

Every morning I’d wake up with no alarm clock, and remember all of my dreams. I started writing them down. The more I wrote, the more I remembered. Sometimes it would take 45 minutes just to write down all the vivid details.

One Friday in January, I had this vivid dream that I was outside a big military building in the 1950s. A mounted air force jet outside, and General MacArthur was at the door. We talked for a minute, then he let me in. I walked down a long empty hallway, then took a right, and walked down another long empty hallway.

At the end of the hallway was a younger Sammy Cahn, in the 1950s, with a full head of brown hair, waving his arms, yelling at someone. (“Goddamn it! What the hell were you thinking?”)

As I got closer, he stopped, turned to me, and said, “Who the hell are you?”

I said, “Sammy, you don’t know me, but I came back from 40 years in the future to tell you that in 40 years, you’re still going to be alive and well and writing songs every day.”

Just like that day in the kitchen, his face went blank. His mask dropped. He said, in that rare nice voice, “Thank you. I really appreciate it.”

Then I woke up.

I wrote it all down.

The next day, a friend of mine called me at the beach and said, “Well... I guess you heard the news?”

“Uh, no. I don’t get any news out here. What’s up?”

“Your friend Sammy Cahn died last night.”

The same night I had the dream.


I didn’t believe in any of that stuff before, but couldn’t help but wonder about that life-after-death stuff you hear about, or maybe ESP, or something. Who knows if I had the dream right before he died or right after, but I still think he came by to say thank you.

Nov 15, 2019
Human Intervention as a Competitive Advantage

The listening algorithm

A year after I started CD Baby, when it was still just me in my bedroom, the CEO and VP of a hugely-funded Silicon Valley online music company contacted me, saying they wanted to fly out to New York to meet me. I said OK, and we met a week later for dinner.

Dinner was a lot of blah blah blah smalltalk, and I wondered what they really wanted. Then they finally got to the real point:

“The reason we flew out to meet you is because we’ve been looking at many music recommendation engines, and the one that’s powering is one of the best we’ve found. Could you tell us a little something about the algorithms and data points you’re using?”

Uh... I was confused, and asked what they meant.

They said, “The music recommendations on your site don’t seem to be sales-driven like Amazon. The music-matching algorithm comes up with incredible recommendations. What software are you using for that?”

Ah! I get it. I smiled and pointed to my ear.

“No software. I just listen to everything that comes in, and recommend other good stuff like it.”

Now they looked confused. “But how will that scale? You can’t just listen to every single album! What will you do when you start getting a hundred albums a day?”

I said, “Maybe hire someone just to listen. I don’t know. I’m not there yet. I’ll worry about it then.”

And that’s what I did. When we were getting a hundred albums a day, it became someone’s full-time job to listen to every new arrival and do the internal recommendations.

Minimizing or Maximizing?

When everyone else is trying to automate everything, using a little human intervention can be a competitive advantage.

The problem is when business owners see it as a cost, instead of an opportunity. Trying to minimize costs, instead of maximize income, quality, loyalty, happiness, connection, and all those other wonderful things that come from real human attention.

You can buy a fancy phone routing system, so people have to listen to 9 options, choose option 5, then listen to 6 more options...

... or ...

You can hire a charming person to pick up the phone on the first ring, and make a great impression.

Which one do you think will win you new fans?

You can put rules into your online forms, so if someone puts a dash in their phone number, or writes “coming soon” as their URL, it tells them they’re wrong and makes them do it over again....

... or ...

You can have new submissions be checked-over quickly by a real person. It’s worth the 10 seconds of human effort, to keep the end-user experience easy but the internal data correct.

It’s fun for techies to try to find the tech solution to everything, but don’t forget that even a tiny touch from a real person can be the best algorithm, and a massive business maximizer.

Who should do the work?

I understand the mindset. It’s saying, “By having our software and our users do most of the work, we can keep our business efficient and scalable.”

But if you want them to pay you, if you want to be more valuable, you have to take on more of that work.

I meet so many entrepreneurs who are convinced their thing will be as big as Facebook, so they can’t afford to have a personal touch for all those billions of users that are going to start flowing through their app.

But by removing all human contact, they’re making their app less valuable. They’ll never get big enough for the question of scale to matter.

Nov 14, 2019
Experiments in music and life

One approach to music is to do whatever you want. Absolutely anything goes. But to me, that’s too free. It’s anti-inspiring because having infinite options is overwhelming.

Another approach to music is to follow tradition. You stay within the guidelines of a genre or style. But to me, that’s too strict and sad. It was someone else’s innovation. To imitate it now with rules and recipes is just nostalgia. It’s uninspired and dishonest.

So my favorite approach to music is in-between. You make up your own rules, and apply them to a piece of music. You know what this is called? An experiment!

  • Experiment with limitations. Write a piece using only two instruments and five notes. Write a lyric using only nouns and no verbs.
  • Experiment with textures. Record an arrangement using only children’s toys or samples of birds.
  • Experiment with density. Write a piece featuring fifty intruments. Then do a solo piece using only your left hand.

I loved learning and applying specific techniques. Like I’d learn a certain way of developing a melody, then go write melodies using that method. I’d learn about re-harmonizing — where you keep the same melody but change the chords underneath, completely changing the mood — then I’d go apply that to all of my songs. Techniques to build tension. Techniques to change time.

With each new thing I learn, I have to try it, and make something. It might not even sound good, but that’s OK. The goal was just to see what happens, so there’s no way to fail. It’s all just fertilizer for future creations.

I’m not an active musician anymore, but now I find that the way I approached music is the way I approach life.

After I sold my company and life was a blank slate, I found that having too much freedom was overwhelming.

But I’m not going to buy into an -ism and follow a set of ancient rules.

So instead I do experiments. I make up rules, and apply them to my life for a while. Like…

  • Experiment with limitations, fear, detachment, or my definition of home.
  • Experiment with fame, boundaries, expanding, quitting, or my self-image.
  • Experiment with vulnerability, commitment, saying yes, or saying no.

I usually try the opposite of whatever I did before.

I still love learning and applying specific techniques. Techniques for conversation. Techniques to stretch time. I’m glad I know how to re-harmonize because there are melodies in my past I can’t change, but I can change the thoughts underneath.

With each new thing I learn, I have to try it. It might not even feel good, but that’s what experimenting is about. The goal is still to see what happens, so there’s no way to fail.

Nov 07, 2019
Cross the world four times

Cross the world four times.

First, in your teens or 20s, to take it all in. See it all, do it all, and learn. Get involved. Stay up all night talking with strangers, everywhere. Kiss and fall and promise to them all. Make lots of mistakes.

Cross the world the first time to fall in love.

The second time, in your 30s, to tell everyone what you’ve learned. You’re full of answers, since you’ve done so much. You know how things should be, since you’ve made all your mistakes. You can see the path clearly, and it’s your turn to lead.

Cross the world the second time to make change.

The third time, in your 50s, to compensate. You realize what a blow-hard you were in your 30s, and how little you actually know. You’ve been humbled. It’s time to make up for years of thinking others were wrong. Pay close attention and listen without judgement for once. Have no answers — only good questions and good ears.

Cross the world the third time to unlearn.

The fourth time, late in life, to witness. To find old friends, and find that they’re gone. To see what’s changed, and what’s stayed the same. To appreciate the young. The world is theirs, not yours. Now you know what happens when you die: everything! Evolution, revolutions, inventions, disasters, so much love, and so many lives. You just won’t be part of it anymore.

Cross the world the last time to say goodbye.

Nov 06, 2019
My old clothes don’t fit

I was uncomfortable, unhappy, and restless. I didn’t want to meet new people, because I felt I was giving the wrong impression. Something wasn’t right. It took me months to figure out the real problem: My clothes don’t fit anymore!

Once I realized this, I had to decide what new clothes would fit the new me. Like many of us, I looked to the style of glamorous and successful people. I should wear what they wear since it works so well for them. I tried on many of their outfits, but nothing fit. That was really disappointing, because I thought that’s why they share their choices with the world — so we can do what they do. I thought it would be that easy.

Eventually, after a lot of searching, I found clothes that are just my size. But I couldn’t get them on! There was no room at all. I’m embarrassed to say I overlooked something obvious. I was trying to wear new clothes on top of the old ones. I didn’t realize I had to completely remove my old clothes before putting on something new.

It was easy to take off my old clothes for a few days, but just having them around made it too easy to put them on again. They were so comfortable! I’d been wearing these things for so many years that they really became my identity. If you put my old clothes on a mannequin, it would look like me. What does that say about me, then? We are what we wear? Clothes make the man?

So, I had to completely discard them. It was sad — I thought those clothes would last forever. I documented them for archive’s sake, then gave them away. I’m glad someone else can use them.

In this transition, before I put on my new clothes, I’m naked.

It feels weird. I’m surprised I’m allowed to go out like this.

Old friends hardly notice, but new people I meet are confused and can’t tell why I’m not wearing something. An outfit would show them how I can help. (And that’s all most people want to know.)

  • A power suit would show I can help their business.
  • A monk’s robe would imply I could help their soul.
  • Explorer’s gear would prove I could lead an adventure.
  • A clown costume might at least make them laugh.

But nothing at all? They probably can’t use me for anything.

I get invited to speak at events, but it’s clear that they really just want the outfit I used to wear. I explain that it doesn’t fit, but they’re upset that I won’t put it on just one more time.

Don’t worry — I’m not going to be a nudist now. That’s inconsiderate to almost everyone. I’ll put on my new clothes soon.

But I’m just sharing this story in case your discomfort might just be that your old clothes don’t fit anymore.

Mannequin photo by Oiluj Samall Zeid
Nov 03, 2019
The art of selfishness

David grew up in St. Louis, Missouri, USA, with five brothers and sisters.

When he was 18, he got accepted to a very prestigious art school in Vienna. Vienna! This was his dream come true! He had wanted this so badly, but never thought he’d actually get accepted. This was an amazing once-in-a-lifetime opportunity.

But his mother was on her death bed. An undiagnosable illness seemed like it was going to take her at any time. All of her children were visiting her every day.

When he mentioned that he got accepted to the art school in Vienna, everyone said, “Well of course you can’t go! You need to stay here with your mother during her final days!”

He was very conflicted and felt horrible about this, but still felt that he had to accept the offer. So he moved to Vienna.

His mother disowned him. His brothers and sisters screamed about his selfishness, and didn’t speak to him for years. Everybody told him what a horrible person he was.

David told his story at the age of 38 and said, “And now, 20 years later, my mother is still alive. I’ve followed my dreams, had a great career and an amazing life, while my brothers and sisters have given up their whole lives to stay by my mother’s bed, still to this day.”

The David in this story is David Seabury, who changed thousands of people’s lives. It’s from his book “The Art of Selfishness”, which I found on my grandmother’s bookshelf when I was 18. I’ve thought about it constantly since then.

Nov 02, 2019
Doors and windows and what’s real

Like everyone, I live in a little house with many doors and windows.

One door goes out to my neighborhood. The local kids come to play with my dog. The elderly neighbors take so long to tell me their stories. I slow down my inner clock to listen.

One window looks out at the nature around me. I’m getting to know this one tree really well. I toss a little dog food out there each day, and watch the local birds and rodents come by to eat it.

One door is just for my son. This door goes somewhere new every time he opens it. I pause what I’m doing and follow him on an adventure. My inner clock stops working through that door.

One door goes to my connections — the people around the world with mutual interests. A dozen people a day knock on this door and say hello. Sometimes more.

One hidden door is for my dearest friends. That one comes all the way inside, anytime.

One skylight looks far into the future. I daydream there a lot.

One little locket looks at the past. I daydream there, too.

But one door is really no fun to open. Whenever I do, I’m horrified at all the shouting. It’s an infinite dark room filled with psychologically tortured people, trying to get attention. Strangers screaming at strangers, starting fights. Businesses put windows there, showing bad things said and done today, because they make money when people get mad.

They say I’m supposed to open that door, because that’s the real world.

But it seems a lot less real than what’s in the other doors and windows in my life.

“Watching the World Go By” photo by Jocelyn Erskine-Kellie
Nov 01, 2019
Benefits of a daily diary and topic journals

You know those people whose lives are transformed by meditation or yoga or something like that?

For me, it’s writing in my diary and journals. It’s made all the difference in the world for my learning, reflecting, and peace of mind.

After 20+ years of doing this, here’s what I do and recommend:

A daily diary

If digital, use only plain text. It’s a standard format not owned by any company. It will be readable in 50 years on devices we haven’t even imagined yet. Don’t use formats that can only be read by one program, because that program won’t be around in 50 years. Don’t use the cloud, unless you’re also going to download it weekly and back it up in plain text outside that cloud. (Companies shut down. Clouds disappear. Think long-term.)

Every day at some point, just open up this diary, write today’s date, then start writing. Write what you did today, and how you are feeling, even if it seems boring.

It works best as a nightly routine. Just take a few minutes and write at least a few sentences. If you have time, write down everything on your mind. Clear it all out. But if you miss a night, make time the next morning to write about the previous day.

This is important because years from now you might be looking back, wondering if you were as happy or as sad as you remember during this time. So don’t only write the drama or dilemmas. Include the daily facts of life.

We so often make big decisions in life based on predictions of how we think we’ll feel in the future, or what we’ll want. Your past self is your best indicator of how you actually felt in similar situations. So it helps to have an accurate picture of your past.

You can’t trust distant memories, but you can trust your daily diary. It’s the best indicator to your future self (and maybe descendants) of what was really going on in your life at this time.

If you’re feeling you don’t have the time or it’s not interesting enough, remember: You’re doing this for your future self. Future you will want to look back at this time in your life, and find out what you were actually doing, day-to-day, and how you really felt back then. It will help you make better decisions.

Just put aside a few minutes to write what you did and how you felt today.

“Thoughts On” journals

There are certain subjects in your life you think about a lot. People, places, hobbies, health, plans, finances.

For each subject that you might have ongoing thoughts about, start a separate “Thoughts On” journal. Whenever you have some thoughts on this subject, open up that file, write today’s date, then start writing.

To give you an example, here are my “Thoughts On” journals as of today:

  • Accounting
  • Addiction
  • Airports
  • Alcohol
  • Ambition
  • Animation
  • AppDevelopment
  • Artist
  • Assistant
  • BeingSocial
  • Blog
  • BookNotes
  • BookPublishing
  • Calendar
  • Carla
  • Changes
  • Chess
  • Chinese
  • Cities
  • Comedy
  • Comparing
  • Computers
  • Conferences
  • Countries
  • Dance
  • Dog
  • Entrepreneur
  • Erika
  • Europe
  • EventStrategy
  • Expat
  • ExploreExpand
  • Fame
  • Fan
  • Friends
  • Goals
  • Gratification
  • Habits
  • Home
  • IdealMe
  • Image
  • Infrastructure
  • Intense
  • Interviews
  • Investing
  • Ireland
  • Kissing
  • LanguageLearning
  • LateralThinking
  • LifeAlgorithms
  • MakeIdeas
  • Manners
  • MobileAppDev
  • Money
  • Music
  • MyPeople
  • Need
  • NewZealand
  • Noise
  • OS
  • Oxford
  • Parenting
  • Phone
  • PhoneNumbers
  • Places
  • Plan
  • Poor
  • Portugal
  • Potential
  • Programming
  • PublicMe
  • RV
  • Regrets
  • Relationship
  • Renting
  • Romance
  • Routine
  • Secrets
  • Sex
  • Singapore
  • Skills2Learn
  • Social
  • Solitude
  • Songwriting
  • Speaking
  • Strength
  • Surprise
  • Teachers
  • Tech
  • ThinkingSelf
  • Thrifty
  • Travel
  • VirtualReality
  • Vision
  • Website
  • WorthDoing
  • Writer

I find it so useful to keep my thoughts on each subject together, because I can see my past thoughts and current thoughts in one place. I can see how my thoughts on this subject have evolved or keep repeating. Sometimes I think I have a new thought on a subject, so I open up the file and write it down, then afterwards I see I had that same thought a year ago and had forgotten about it. If you care about your thoughts, keep them.

They can be tiny. Like you see I have one on airports. I don’t have many thoughts on airports. I don’t fly that much. But I found that once or twice a year, when waiting at the gate, I had thoughts on the subject, so I’d open that file and start writing.

I’ve considered making one for every musician, album, book, or film that’s had an impact on me, that I’d like to think more about. Why not? I admire the way that a good critic puts in hours of reflection on each piece, thinking deeper about something they’ve just taken in.

I especially like my “Regrets” journal. Whenever I do something I regret, I write it down there, noting why I regret it, what I wish I would have done instead, and how I hope to prevent this in the future.

Ask yourself questions, then question your answers.

Whether in your daily diary, or the “Thoughts On” journals, I find the single most useful thing has been using it as a place to ask myself questions, and answer them.

If I’m planning on doing something, I ask myself what I hope to get out of it, why, and whether there are other ways to get what I want.

When I’m feeling conflicted, especially, I’ll ask myself a bunch of questions to work through my feelings, looking for the source of the conflict, then ask myself more questions around the clash in values, and work through other alternate ways I’d like things to be.

I answer with my initial thought first, but then question it afterwards with skepticism, and consider different perspectives. I hear this is similar to cognitive behavioral therapy — and I’ve been meaning to learn more about that. But whatever you call it, I think it’s been the single most important thing to my intellectual and emotional development.

Almost all the thoughts I have on any subject are the result of writing in my diary and journals, then questioning myself and working through alternate ways of thinking about it, and finally returning to the subject days or months later with a clear head and updated thoughts, seeing how they’ve changed or not over time.

I hope it helps you too.

Oct 31, 2019
How I got rich on the other hand

I don’t usually talk about money, but a friend asked me what it was like to get rich, and he wanted to know specifics, so I told him my story.

I had a day job in midtown Manhattan paying $20K per year — about minimum wage. On weekends I would earn $150 per day performing circus shows for kids, though I’d spend about $50 in bus fare to get to the gigs. I was sharing a three-bedroom apartment with two other roommates in Queens, so our rent was $333 per month each. I made peanut butter sandwiches for three meals a day, and at night maybe some eggs. I never ate out, and never took a taxi. My cost of living was about $1000/month, and I was earning $1800/month. I did this for two years, and saved up $12,000. I was 22 years old.

Once I had $12,000 I could quit my job and become a full-time musician. I knew I could get a few gigs per month to pay my cost of living. So I was free. I quit my job a month later, and never had a job again.

When I finished telling my friend this story, he asked for more. I said no, that was it. He said, “No, what about when you sold your company?”

I said no, that didn’t make a big difference in my life. That was just more money in the bank. The difference happened when I was 22.

It’s not how much you have. It’s the difference between what you have and what you spend. If you have more than you spend, you’re rich. If you spend more than you have, you’re not. If you live cheaply, it’s easy to be free.

Magicians wave one hand around to get your attention, while the other hand does the trick. To be smart, watch the other hand.

Oct 30, 2019
When in doubt, try the difference

If you’re in doubt about something that’s not in your life, try it. Things are so different in practice versus in theory. The only way to know is to experience it yourself.

Try it examples:

  • Pursuing a new interest?
  • Moving somewhere very different?
  • Quitting your job to go freelance?

Err on the side of yes. Try it. If it was a mistake, at least you’ll know first-hand, instead of always wondering.

If you’re in doubt about something that’s in your life already, get rid of it. Not just things, this goes for identities, habits, goals, relationships, technology, and anything else. Default to not having it, then see how you do without.

Get rid of it examples:

  • Relationships that bring you down
  • Goals you’re not pursuing
  • A career that’s plateaued

Err on the side of no. Get rid of it. Start with a clean slate, If it was a mistake, you’ll get it back with a renewed enthusiasm.

(The common thread is to make the change, to know first-hand.)

Get rid of everything examples:

  • Erase your phone and computer. Re-install the operating system from scratch. Don’t restore from the backup — not even your contacts. Only add back people who contact you. Don’t install any apps unless you can’t do without them.
  • Put everything you own into storage. Move somewhere small and simple, bringing only what you’d take on a two-week trip. Only when you absolutely need something, go get it out of storage. After a year, sell all that stuff in storage.
  • Move across the world. Start from scratch with a new career, new friends, and new approach to life. Every time you start to do something out of habit, interrupt the pattern and try the opposite way instead.

(These are my favorite. I actually do these things regularly. I love simplifying.)

Oct 28, 2019
Why experts are annoying

When someone becomes an expert at something, you know what else they become? Annoying.

At a restaurant, your designer friend complains about the font on the menu, your musician friend complains about the background music, and your manager friend complains about the service. Why?

The problem is that their expertise makes them annoyed. They’re trained to spot errors. They’re so aware of what’s wrong. Even worse, they know exactly how to fix it. They learned the techniques to make things great, so they’re angry when someone didn’t do the obvious solution. They get so frustrated that they can’t focus on their meal, because now they really want to fix the problem.

These things don’t bother the rest of us. We’re easier to please. Good is good enough.

So only those who are the most upset, and know how to improve things, do the hard work necessary to make things great. The dissatisfied ones go make things better for all of us.

Why are experts annoying? For our benefit. They get mad so that we don’t have to.

Next time your friend is upset and ranting about design, politics, layout, economics, or something else you don’t care enough about, thank them for taking on the burden of knowing how to fix things, and remind them that it’s up to them to make it better.

Oct 27, 2019
What you learn by travelling

I wanted to learn about the world, so I went travelling.

People in the east are so graceful, I felt like an inconsiderate pig.

People up north are so serious, I felt like a lightweight clown.

People down south are so laid-back, I had to escape north again.

The way we define ourself is all relative to our surroundings, right? However we differ from the people in our home town is how we define ourself. That’s where we shape our self-identity, growing up. Those are our defining traits.

But when we go to a different place, the relative comparisons collapse. Traits like speed, ambition, independence, bravery, and humor — they’re all relative.

Back home I’m considered quiet. Here I’m considered loud.

Back home I’m a slacker. Here I’m a workaholic.

Back home I’m normal. Here I’m strange. Or vice-versa. So how do I define myself now?

I always want to know why a culture is this way. What’s the difference? What are the core beliefs? So I ask questions and observe.

On the surface and from a distance, I see their actions. But deeply and closely, I see my reactions.

I want to learn about the world, so I keep travelling.

About the world, I learn a bit. About myself, I learn a lot.

Oct 26, 2019
PostgreSQL example of self-contained stored procedures

First, see my previous article about PostgreSQL functions at That article gave tiny examples, but no finished working code.

This week, I wrote a shopping cart to sell my books directly from my own site.

So I took a couple extra hours today to put my code into public view, so anyone can play around with it. See, to browse, download, and try it.

It’s a working self-contained shopping cart / store. It’s a very concrete example of using stored procedures to keep all the data logic together in one place. You can use it from JavaScript, Python, Ruby, or any language you want, since all the functionality is in the database itself. It works.

If you have any questions, or want to tell me how stupid I am for doing this, email me.

Oct 25, 2019
Mastery school

Here’s an idea: Create a little school somewhere remote. School of what? School of mastery.

A place for anyone who wants go focus on a skill of their choice, surrounded by other people doing the same, and a few coaches — experts on the craft of mastery — to offer help and guidance.

This uses Salman Khan’s proposal to “flip the classroom” so that the core of learning is done in independent study, using online materials.

Since the teachers are all online, the local coaches just help guide each student’s path to mastery. There are many great books on this subject, like…

So you can see how the general skill of guiding and coaching talent, in any field, could be the best focus of the on-site staff.

The school should be located somewhere that fits with the story we tell ourselves about going away to focus. Somewhere that’s a desirable location, yet still somewhere with income inequality, where a school bringing a little business and fast fiber internet to a remote location would be appreciated. All the staff except the coaches could come from the local community.

Some shared resources like a good camera and microphone, a few computers, a video library to save bandwidth, and a chef making meals for everyone.

I imagine this could be as small and simple as a big house in the country, or a few cabins nearby.

Why attend?

  1. To get away somewhere you can focus without distraction — a show of dedication and focus
  2. To be around other serious focused learners, inspiring eachother
  3. To have the help of coaches that are great at helping anyone learn anything. They are experts in the skill of practice, learning, and mastery.

So, you go there to work on your thing, whatever it is.

  • You learn from online materials, books, and whatever it takes.
  • You practice and create as much as possible.
  • You're surrounded by kindreds and assistance.
Oct 24, 2019
Monthly self-expansion project

Here’s an idea: Every month, pick something you hate or know nothing about, and get to know it well. Spend a few hours per week, for an entire month, just learning about that subject. Why?

The idea is inspired by a very successful friend of mine who is regrettably closed-minded. She hates everything that isn’t European, sophisticated, and familiar. Culture of India? Hates it. Chinese opera? Hates it. West African music? Hates it. Any mention of any of these things, and she completely shuts down. Appreciating them is not an option. I tried to play her my favorite Indian music, and West African music, but nope. Just a few seconds into it, she asks me to shut it off.

It made me realize that some of the greatest joys in my life are the things I used to hate, or know nothing about, and now have grown to love. Read my post “Loving what I used to hate” for my story about that.

So I thought: Instead of letting it happen accidently or randomly, why not be deliberate about it? Some ideas of things to study for a month would be…

If it’s learning a skill, read Josh Kaufman’s First 20 Hours and use that approach.

While you might lean towards things you’ve always wanted to learn about, I think it’s more interesting to ask yourself, “What do I have absolutely no interest in?” or “What sounds repulsive to me?”, then aim to understand one of those things. Start with a kind of music you hate, or a part of the world that sounds unappealing to you. That’s where the real self-expansion happens.

Whenever we learn about something, we learn to appreciate it. So it’s most rewarding if it’s something you previously had no appreciation for.

I like this idea a lot, and plan to do it soon.

Oct 23, 2019
Living according to your hierarchy of values

My “daily” blog was silent the last four days, because I took my kid on a spontaneous trip to another country. No phone. No computer. I gave him my full attention every day from when he woke me in the morning to when we fell asleep together at night. It was great.

I thought for a minute about the importance of my commitment to post here daily. But nope, being with him is more important than writing.

Upon returning, I considered heading off by myself on a 10-day trip, balancing writing and exploring another culture. But after sleeping on it, I realized that no, writing is more important than exploring.

Once you realize that one value is more important to you than another, you have to ask yourself if you’re living accordingly.

What’s ultimately more important to you?

  • Learning? Or creating?
  • Money? Or time?
  • Expanding? Or focusing?
  • (… etc.)

Once you know which takes top place, consider taking it to an extreme, to its logical conclusion, and optimizing your entire life around that top priority, letting go of almost everything else.

If the idea sounds unfulfilling, try re-ordering your priorities, and do the thought experiment again.

(That’s the subject of my next book, “How to Live”, which is my top writing priority right now, and so much fun!)

Oct 22, 2019
How to ask your mentors for help

I have three mentors.

When I’m stuck on a problem and need their help, I take the time to write a good description of my dilemma, before reaching out to them. I summarize the context, the problem, my options, and thoughts on each. I make it as succinct as possible so as not to waste their time.

Before sending it, I try to predict what they’ll say. Then I go back and update what I wrote to address these obvious points in advance. Finally, I try again to predict what they’ll say to this, based on what they’ve said in the past and what I know of their philosophy.

Then, after this whole process, I realize I don’t need to bother them because the answer is now clear.

If anything, I might email to thank them for their continued inspiration.

Truth is, I’ve hardly talked with my mentors in years. None of them know they are my mentors. And one doesn’t know I exist.

Oct 17, 2019
When you win the game, you stop playing

Someone asked me today why I don’t charge money for the things I do.

Why don’t I have ads on my site? Why don’t I exploit my assets and pursue some profitable things?

I already did that.

I made more than I’ll ever be able to spend.

What do you do when you win a game?

You stop playing, and go do something else.

Oct 16, 2019
Digital pollution

You couldn’t just roll down the street leaving huge piles of garbage everywhere you go, making life slower for everyone as they climb over your mountains of junk, just to get on with their life. You’d feel bad about it, right?

That’s how I feel about the digital things we put out into the world: websites, apps, and files.

I prefer coding everything by hand, because I don’t like the huge piles of garbage that the automated generators create. These programs that generate a website, app, or file for you spit out thousands of lines of unnecessary junk when really only 10 lines are needed. Then people wonder why their site is so slow, and they think it’s their phone or connection’s fault.

Yesterday I needed to make a little vector logo. Two lines and two triangles. I tried to use a couple different vector drawing programs but they saved it as hundreds of lines. I knew it could be simpler, so I read up on SVG and made exactly what I wanted:

 <svg height="54" width="54"> <defs><style type="text/css"><![CDATA[line,polygon{stroke:black;stroke-width:4} polygon{fill:black}]]></style></defs> <line x1="2" y1="2" x2="2" y2="52" /> <line x1="52" y1="2" x2="52" y2="52" /> <polygon points="2,2 27,27 2,27" /> <polygon points="52,2 27,27 52,27" /> </svg> 

Much better! 95% smaller file size, and the joy of making something by hand instead of having it done for me. But I think my biggest joy is eliminating the digital pollution that the auto-generated one created. It makes everything faster, easier, and cleaner for anyone involved. 95% less junk over the wires.

Same thing with the EPUB file for my new book. Today I spent the day creating the EPUB’s XML and XHTML by hand, instead of using a generator. I love the manual control and again - 90% smaller file size.

This makes me unreasonably happy. It feels like cleaning up the neighborhood. Or at least my yard.

(And I love it when people notice how fast my site loads.)

Oct 15, 2019
Cut out everything that’s not surprising

This is my advice to anyone writing something for the public — especially a talk on stage.

People listen to a talk, or read an article, because they want to learn something new.

They want a little “oh wow” moment. “I never thought of it that way before.”

People only really learn when they’re surprised. If they’re not surprised, then what you told them just fits in with what they already know. No minds were changed. No new perspective. Just more information.

So my main advice to anyone preparing to give a talk on stage is to cut out everything from your talk that’s not surprising. (Nobody has ever complained that a talk was too short.)

Use this rule in all your public writing. If you already found something surprising in what you’re presenting, then remove everything else. If you haven’t found something surprising about it yet, keep looking until you do.

Oct 14, 2019
Heed your fears

People often ask me how they can get over their fears. For example, they are scared to quit their job and start a business.

I think they want me to say something to make their fears go away. So my advice is pretty disappointing.

We should pay attention to our fears. They often have good reason.

Instead of ignoring them, we need to address them. Break it down, and look deeper into what’s inside them. Address and mitigate the specifics. It usually means you need to learn a little more. Look before you leap.

Always ask, “What’s the worst that could happen?” Because sometimes the only problem was not realizing that the worst case scenario isn’t bad at all.

But don’t just tell yourself to get over it or ignore it.

Oct 13, 2019
Daydreaming is my favorite pastime

Somewhere in our past, we were told it’s bad to daydream, because it meant doing nothing — staring out the window — instead of doing what we’re supposed to be doing. To admit we’re daydreaming felt like it needed an apology.

But now I’ve finally embraced it. Deliberate daydreaming is my favorite pastime.

About half the time that I used to read a book, I now just skip the book, and sit there daydreaming instead. And I almost never watch videos anymore. I just close my eyes and daydream.

I find it most fun to ask myself a big question:

  • Which were the top three best times in my life so far?
  • What are my biggest regrets?
  • What would I write a screenplay about?
  • If I had the magic lamp, what would be my three wishes?
  • What does the most ambitious version of myself look like?
  • What about the least ambitious version of myself?
  • How can I be a better dad?
  • At what would I most love to become an expert?
  • Is there anything I can’t do without?
  • How would my life be different if I was blind? Deaf? Paralyzed?

We’ve all had plenty of input. It’s fun to let your mind direct its own entertainment.

Oct 12, 2019

I don’t know why I have this rebellious nature. I tend to want to be the opposite of my surroundings.

At serious formal events, I can’t stop laughing inside. At crazy festivals, I want to hide and read a book.

My ambitious friends bring out the slacker in me. My lethargic friends make me feel like superman.

When I moved to Boston, as a teen, and everyone was wearing black, I dressed in only white. I remind new-agey people of the scientific method.

Is it a desire for balance? To represent what seems under-represented in this situation? Is it my love of seeing the other side?

I hear I’m not supposed to react like this. I’m supposed to be the same, no matter what’s around.

But I’m not the same from day to day, even when alone. I rebel against myself, too. If I’ve been thinking or acting one way for too long, I try another way.

It’s worked pretty well for me so far. I’m super-motivated by the horror of seeing the opposite of what I want.

  • Seeing someone waste their talent motivates me to get back to practicing and creating.
  • Seeing a person in horrible health motivates me to be healthy.
  • Seeing someone freaking out motivates me to be calm.
  • Seeing someone being selfish motivates me to be generous.

The list goes on. It’s been net positive. So, I’m not fighting it for now.

(P.S. I’ll never argue against preserving nature.)

“A Man Feeding Swans in the Snow” photo © Marcin Ryczek.
Oct 11, 2019
Where we do and don’t want automation

I used to use Gmail. But one day, as I typed my mother’s email address into the “To:” field, Google popped up a prompt asking if I also wanted to CC my uncle. That was so invasive and creepy that I deleted the account immediately and never used it again. I don’t want automated intelligence in my private email.

My friend lives in a home full of the smartest technology, and loves getting all the new smart things, but he drives a deliberately retro old car with no computer chips. He loves to tinker with his car, and wants to do any maintenance himself.

Another friend lives in a tech-free rustic cabin with no screens, but drives a Tesla.

I do everything on a broken old Linux laptop, using only the command line, usually offline, nothing in the cloud. I think it’s because I don’t want any outside automation or intelligence in the work that matters to me.

When software is described as “auto-”, “smart”, or “intelligent” it means that somebody else put their rules into it. But I don’t want my computer to do anything I didn’t explicitly tell it to do. It shouldn’t change what I typed unless I tell it to. It should never guess or predict what I want. I want full manual control.

On the other hand, I don’t mind if my phone does these things, because I don’t care about my phone much. And I would love a high-tech car, full of smart AI automation, because I’m not a car aficionado.

At first I thought that an expert at something won’t want assistance. But no, of course, auto-pilot for airline pilots, and IDEs for programmers.

So I think it comes down to:

  1. how much of an expert you are at controlling this thing yourself
  2. how much you still enjoy doing it
  3. if you want the kind of assistance it provides

Any thoughts on this subject? I’d love to hear another point of view.

Oct 10, 2019
Human nature to focus on the one bad thing

Today my bus was delayed, and I was really annoyed.

Also, I got a really nasty email, which put me in a worse mood.

No, wait, I should give the full story.

It takes two busses to get from the airport back to my house. The first bus leaves once per hour. That connects to a second bus that leaves every five minutes.

Today I was super-lucky and got to the first bus just before it left. If I would have emerged from the airport a minute later, I would have waited an hour for the next one.

But then the second bus was delayed, and I had to wait about ten minutes. That’s what got me really annoyed, and feeling like today was a bad day.

Then I got home and downloaded my emails. There were about fifty really nice ones, and one nasty one. That’s what put me in a worse mood.

I didn’t remember until later how lucky I was to just make that first hourly bus. Then had to laugh at myself for being upset about waiting ten minutes for the next one, and upset about one stupid email among a bunch of nice ones.

It’s human nature. We all do it. Life is wonderful, and we focus on the one thing that’s not.

Oct 09, 2019
Back and forth between super-hot and super-cold

The most relaxed feeling I know is after going back and forth between a super-hot pool and super cold pool.

Stay in the super-hot pool until you can’t stand it. Then go in a super-cold pool until you can’t stand it. Repeat that a few times, and you’ve never felt so relaxed.

Today I went to the Löyly sauna in Helsinki, Finland. I stayed in the super-hot sauna room until I couldn’t stand it. Then I’d jump in the icy ocean until I couldn’t stand it. I went back and forth like this for almost two hours. It’s so wonderful.

There was also a medium-hot sauna room. I tried that for a while, but it just felt “eh” — neither here nor there — not as fulfilling or relaxing as the extremes.

I like trying different ways to approach life.

I’ll maximize my input for a while — say yes to everything, meet everyone, go everywhere. Then I’ll maximize my output for a while — say no to everything, and just focus on my work.

I’ll do the domestic life for a while — with a house, car, dog, furniture, stocked kitchen, and stuff. Then I’ll give it all away, until I’m back to the one suitcase of the things I really need.

And yes, I tend to do each one until it feels like I can’t stand it anymore.

It’s fun to push the boundaries — to explore the edges — to see what I can do. I’ve never been interested in pursuing a normal life. There are enough people doing that. More growth and discovery seems to happen when I’m uncomfortable.

Some people think it’s strange, and ask why I feel the need to be so all-or-nothing. They ask why I don’t just find the middle ground. (Neither here nor there.)

But there’s something more fun and fulfilling about experiencing the more interesting extremes. Knowing I can live in these different scenarios is ultimately more relaxing.

Oct 08, 2019
Err on the side of action, to test theories

I spend a lot time thinking of alternate ways to approach life.

I re-consider my hierarchy of values.

When values change, the plan of action needs to change, too.

For example, if I decide that personal growth is top priority, then I plan a life pushing outside my comfort zone. But if I decide that creative output is top priority, then I plan a tranquil life without obstacles, so I can just create.

But the only way to decide — to not be Buridan’s donkey — is to go give it a try.

There’s a huge difference between in-theory versus in-practice. If you’ve been deliberating on something for a while, get it out of your head, and into the world.

If it turns out to be a mistake, that’s fine. At least you’ll know it’s a mistake in fact, instead of just in theory.

Oct 07, 2019
Blowing off work to play

What do you call it when you skip school or work for a day, to do whatever you want instead? In America, we call it playing hooky. In England, we call it skiving. (Got another word for it?)

Some of my best, most productive, and enjoyable days have been while playing hooky.

I think it’s a healthy practice, to occasionally blow off a previous commitment, and do whatever you want instead. It’s a great reminder that you’re the boss of your life.

But it’s interesting how productive I am on those days.

When I think back about the times in my life where I got the most done, created the most, or had a major breakthrough in some aspect of my life, it was often while I was supposed to be doing something else.

For example: I’d sign up for a three-day conference, show up to registration, decide I don’t want to go, then sit in my hotel room, uninterrupted, and get some great work done for three days.

This has happened multiple times. I really should stop signing up for conferences!

Or… Could we use this as an effective productivity technique?

  1. Sign up for something — a time commitment.
  2. Put aside the time to do it.
  3. When the day comes, feel the tension between what you said you would do, and what you really want to do.
  4. Blow it off, and do what you really want instead.

Maybe the productivity comes from the fact that the time has already been put aside, so I suddenly have free time to do what I really wanted.

But I suspect that when I feel that tension between the obligation and desire, it amplifies the difference, and makes it clear to me how badly I want to do this other thing. Then that amplified desire leads me to be more intense and focused in my actions.

Oct 06, 2019
The joy and strategic wisdom of ignoring plans

I took my 7-year-old to London today. I made two plans: if it rains, we go to a museum, if not, we go to the zoo.

But when the train arrived in London, he said he didn’t really want to do either one. So we just walked with no plans.

We immediately ran across some random building with a big art installation on its side. There was nobody around. We played there for a long time.

At each intersection, we just went whichever way looked most interesting. He lept around park benches with some kids from Croatia, playing tickle games. He found a huge cardboard box in the trash, and kept it around him like a turtle shell, as we walked through the city. He found a discarded paint brush and twirled it around his fingers for the rest of the day.

We were in front of the theater with the musical “Wicked”, just as they were about to begin. We bought last-minute tickets, 8th row center, and watched the show. He held hands with a girl sitting next to him.

I’m so glad we didn’t follow any plans today. We make plans to make the most of our time — but thinking again about that idea, that doesn’t make sense, does it? Unless we’re actually shut out of great things for lack of planning, then following no plans is the ideal way to make the best of each moment. Every moment provides new information, which changes the situation. Then we can act on what we know now, instead of what we previously predicted.

I don’t regret having plans, because sometimes following the plan is the best choice. So I guess the lesson is to make plans, but feel free to ignore them — to see them as an option, not a requirement.

After eight hours of walking, we took a night train home. Tucking him into bed, I asked what was his favorite part.

“The cardboard box.”

Oct 05, 2019
Tour -isms

Since I’m living in Europe now, I thought it would be good to tour everywhere in Europe, and get to know it better.

I’m not into seeing the sights. I don’t take photos. What I want is to get to know the mindset, the world-view of each place. The philosophy.

So I wondered if there’s a way to tour philosophies directly. What if, instead of touring places, we toured ideas? Can I tour the “-ism”s?

My collection of Very Short Introduction books includes:

  • Abolitionism
  • Agnosticism
  • Anarchism
  • Anglicanism
  • Antisemitism
  • Atheism
  • Buddhism
  • Calvinism
  • Capitalism
  • Catholicism
  • Communism
  • Confucianism
  • Epicureanism
  • Existentialism
  • Fascism
  • Feminism
  • Fundamentalism
  • Hinduism
  • Humanism
  • Judaism
  • Liberalism
  • Methodism
  • Modernism
  • Monasticism
  • Mormonism
  • Multiculturalism
  • Nationalism
  • Neoliberalism
  • Paganism
  • Pentecostalism
  • Populism
  • Post-colonialism
  • Post-modernism
  • Post-structuralism
  • Progressivism
  • Protestantism
  • Puritanism
  • Racism
  • Romanticism
  • Scepticism
  • Secularism
  • Sikhism
  • Socialism
  • Stoicism
  • Surrealism
  • Terrorism
  • Utopianism
  • Zionism

Now that’s my kind of tourism!

Oct 04, 2019

My friend has a huge crush on someone.

He showers her with attention and appreciation. He remembers her preferences, and constantly gives her thoughtful gifts.

He thinks he’s being considerate, but he’s actually being inconsiderate. Meta-inconsiderate.

By holding her up on a pedestal — by making it clear that he looks up to her — he’s making her look down on him.

People want a romantic partner that’s a “catch” — someone almost out of their league. We want a good deal. We want to win someone.

By chasing her relentlessly, he’s denying her the pleasure of desire.

He’s not letting her dance. Since he keeps pushing forward, there’s nowhere for her to go but backward. He’s not letting her come to him.

Being superficially considerate can be deeply inconsiderate. Doing the opposite is often ultimately more considerate. I call it meta-considerate.

Meta-considerate by contrast:

It’s considerate to not bore my friends with my problems. But it’s meta-considerate to tell them my problems, to let them feel needed and helpful, to let them know they’re safe to do the same.

It’s considerate to greet someone with a smile. But it’s meta-considerate to not smile until they’ve said something, so they can feel that smile was sincerely for them, not presented to just anyone.

It’s considerate to tell a white lie. But it’s meta-considerate to tell the uncomfortable truth.

More meta-considerate examples:

  • The jazz club hidden behind an unmarked door.
  • The meticulous craftsman that has a 9-month waiting list because he custom-makes every order himself.
  • Musicians like Miles Davis, Joni Mitchell, and Bob Dylan, that gave nothing but the music, and didn’t ask for your love.
  • Being silent in conversation, to let your friend fill the space and share more.

Our shallow wants and deeper needs are often opposite.

Oct 03, 2019
Daydreaming the downside, for once

A few years ago, I thought it would be fun to get into camping.

I live in New Zealand! How can I not? I daydreamed about it, picturing how much fun it could be. I read a book about it.

I carefully picked out then bought some highly-recommended gear: a tent, two sleeping bags, two air mattresses, and a light backpack.

We used it once. It’s still in my garage.

Last year, I thought it would be fun to get a Maschine.

A new way of making music! I daydreamed about it, picturing how much fun it could be. I read about it and watched videos about it.

After a few weeks of this, I felt the time was right. I bought one. I played with it a while for the first day, then got back to my normal life, intending to spend more time with it. But I never did.

Every day I would look at it, thinking I should use it. After half a year, I gave up, and gave it to a friend.

Last week, I thought it would be fun to get a new bicycle.

I’ve never tried a carbon frame, modern gearing, or any of the cool new developments in bicycle tech. I live in Oxford, a cycling city! How can I not?

I’ve been daydreaming about it, picturing how much fun it could be.

Wait! Hold on. Have I learned nothing?

So I tried picturing the downside, instead.

I pictured myself not using it, like the camping gear, Maschine, and other things I didn’t mention here. I remembered the pain of guilt, regret, and waste. The conflicted feelings of wanting this thing, but not quite enough.

And I decided against it.

That said, I’m not sure what to conclude.

  • The only mistake was buying instead of renting?
  • Give up on trying new things, and just amplify my current focus?
  • Daydream and learn all about new things, but stop thinking I need to own them? (Awareness is enough for me?)
  • Or maybe the mistake was giving up? Building new habits takes time and effort. After that initial challenge, my life could be richer by the expanded activities in my repertoire.
  • Something else?
Oct 02, 2019
Where to find the hours to make it happen

When you experience someone else’s genius work, a little part of you feels, “That’s what I could have, would have, and should have done!”

Someone else did it. You didn’t.

They fought the resistance. You gave in to distractions.

They made it top priority. You said you’d get to it some day.

They took the time. You meant to.

When this happens, you can take it two ways:

You could let that part of you give up. “Oh well. Now I don’t need to make that anymore.”

Or you could do something about that jealous pain. Shut off your phone, kill the distractions, make it top priority, and spend the time.

It takes many hours to make what you want to make. The hours don’t suddenly appear. You have to steal them from comfort. Whatever you were doing before was comfortable. This is not. This will be really uncomfortable.

The few times in my life I’ve made a real change like this, it felt awful on the surface. I wasn’t shallow-happy about it. I wasn’t smiling. I was annoyed and fighting it inside, but on the outside I did the work. And in the end, got the deeper satisfaction of finishing.

Oct 01, 2019
Your heroes show which way you’re facing

People with many interests often ask my advice on which industry or career path they should follow.

Years ago, I felt I was just a programmer and entrepreneur. Yes sometimes I write a tiny blog post sharing what I’ve learned, but that’s just something on the side.

But something never felt quite right about this. I spend most of my time writing, very little time programming, and hadn’t started a business in years. Still, I kept saying I was a programmer and entrepreneur, and felt I should really spend more time doing it.

But everything changed when I asked myself a question:

“Who are my heroes?”

I thought, wrote them down, then realized they were all authors! Basically, look at my list of favorite books, and there are my heroes.

The people I look up to the most… The people I’d most like to meet… The people I’d most like to emulate are not entrepreneurs, and not programmers — just writers.

So, that day, I realized I actually want to be a writer.

I re-arranged my hierarchy of interests. Yes I enjoy programming, and yes I’ll probably start another business. But really my main love and top priority is writing.

How about you? Who are your heroes? Does that help you see which way you’re actually facing?

Sep 30, 2019
Don’t quote. Make it yours and say it yourself.

Which sounds better to you?

“In his best-selling book on behavioral science, Thinking, Fast and Slow, Nobel-prize winning psychologist Daniel Kahneman said, ‘Nothing in life is as important as you think it is when you are thinking about it.’.”

… or just saying it:

“Whatever’s on your mind is not as important as it seems.”

When I first started reading a lot of books, I started quoting them a lot. When bringing up an idea in conversation, first I would mention its source — the book, the title, the author, and the subject of the book — before finally saying the idea.

After far too many times hearing myself referencing this book and that book, always naming titles and authors, I realized it was a lot of unnecessary clutter. I could see my listeners waiting for me to get to the point. It was inconsiderate.

Then I started noticing how annoying it was to read books that do the same thing. It’s really common in these pop non-fiction books I like: “This person said this thing. That person said that thing.”

It got me wondering: Why don’t we just say the idea, instead of referencing and quoting it?

I think there are a few reasons:

  1. It feels like stealing. It’s their idea, not mine. But all ideas come from somewhere. Maybe they were paraphrasing it from someone else.
  2. School teaches us to reference. But we’re not trying to impress a teacher anymore. And every unnecessary fact dilutes our point.
  3. By quoting someone else, we can easily disavow the idea if attacked. If someone says it’s wrong, we can avoid responsibility and say, “Don’t look at me! It’s his idea, not mine!”

So instead, I go the other way now.

If I hear an idea, have considered it, and integrated it into my beliefs, it’s mine. I’ll say it succinctly in my own words, and stand behind it. Like adopting a child, I will take care of this idea and raise it as my own. If anyone wants to know the source, I’ll be happy to tell them.

I highly recommend this. Stop referencing. Stop quoting. Paraphrase. Internalize it. Make it yours. Tell me what you think, not what someone else thinks.

Sep 29, 2019
Have a private email account

I used to like the internet. I thought it was cool, creative, wild, untamed, expressive, decentralized, and educational. I guess it was, back then, but now? I kinda hate most of what’s out there.

I don’t like social media, either. Staged photos, and people trying to get a reaction. Noise, hype, and drama. It makes me want to avoid the internet completely.

Then I thought about what I do like.

My email inbox is really nice. It’s only people I like, who are emailing me personally. No lists.

I highly recommend setting up a private email address.

Use Fastmail, Posteo, Mailbox, or any similar service where you actually pay $1-$3 per month and in return get a completely ad-free spam-free wonderful email experience.

Then never give this new private email to anyone except dear friends and family.

Let your old Gmail collect the junk. The people you really care about will use the new one, so you won’t need to check the old one much anymore.

It feels nice to have a notification mean something again — to only get one or two emails a day, and know that they are really for you. Or, if you don’t get any notifications, then nothing you really care about has arrived — so no need to check.

Most days I don’t look at the web or any apps. I just write, text friends, call friends, and check email. That’s enough.

Sep 28, 2019
Future posthumous autobiography

I’ve started writing my autobiography. I’ll keep writing it for the rest of my life. It’s private now, but will be released the week I die.

I’ve written the last chapter, which is more of an afterword. (“Now I’m dead.”) So now I will just keep writing the middle chapters.

My assistants, family, and friends will have instructions on how to publish it as soon as I die. A few clicks and commands and it’s published in all formats, print-on-demand, and ready to go the same day.

So by the time you hear the news that I’ve died, the full story — the book of my life — will be ready to read. I think that would be a good goodbye.

Don’t worry : I don’t plan on dying for a long time. My health is great and all is well. This is just my version of the old advice to “write your own epitaph”. I realized I can do better than that.

And I wish the people I care about would do the same.

Sep 27, 2019
What I did belies why

Imagine you host a dinner party with two doctors and two accountants. You introduce the doctors to each other and the accountants to each other, assuming they’d have the most in common.

But actually one doctor got into it because her mother died unnecessarily of medical neglect, and she’s on a mission to make sure that never happens again. The other doctor is in it for the money.

And actually one accountant got into it because her dad’s family business was the victim of embezzling, and she’s on a mission to make sure that never happens again. The other accountant is in it for the money.

You can’t assume the reasons why people are doing what they do.

I learned this slowly and uncomfortably after I sold my music distribution company. Knowing I had a successful exit, people assumed I was an entrepreneur, and wanted me to tell them how to be a better entrepreneur. They asked me to mentor at business schools, where people would bring in PowerPoint presentations showing their financial projections, and talk about raising rounds of financing, and all this stuff I had never dealt with and knew nothing about.

It took me a long time to realize that, like the doctor and accountant story, I must have looked like an entrepreneur from the outside. Yes I founded, grew, and sold a company. But really all I wanted to do was to help musicians. I could have done it by promoting concerts, or being a record producer, or donating to a musicians’ charity — but in my case I built a distribution system for those who had no other distribution. So technically yes, I was an entrepreneur, but it seems I didn’t have much in common with all these entrepreneurs I was meeting. (When I met musicians, it was always such a welcome relief!)

I still think of everything I do as art, not business. It’s personal expression, creative exploration, testing out ideas just to see what happens.

Writing a song isn’t that different from writing computer code. It’s all just having a little vision or spark of an idea, then seeing how you can make it happen — for its own sake.

Starting a band isn’t that different from starting a company. It’s something you do when you’re unable to make your creative vision happen by yourself.

I’ve never done anything just for the money. It’s always been secondary, and always just happened as a side-effect of following my interests. So I don’t have any advice for people who are trying to make money. I don’t know what that’s like.

This is the main reason I stopped doing interviews four years ago. Most interviewers just seemed to want to ask my business advice. I’m feeling ready to do interviews again, as long as we can talk about creativity, identity, exploration, learning, unlearning, communication, cycling, culture, psychology, and all kinds of other things. But I’m not up for talking about business.

Don’t confuse the medium with the message.
Don’t confuse the tool with the goal.
Don’t confuse the vehicle with the path.

Sep 26, 2019
Would you make your art if you were the last person on earth?

Musicians, photographers, writers, and artists of all sorts:

Would you make your art if you were the last person on earth?

For me, it’s an immediate YES — of course! In fact, it might make the experience even better.

A musician friend asked me this question, and was freaked out by my answer. She said she can’t even imagine a world-view like mine. How could I possibly want to make music if there was no one to hear it?

She said, “Ultimately, everything I do is for other people.”

I said, “Ultimately, everything I do is for myself.”

When I’m creating anything, I do it mostly for my own curiosity — to see how I can develop this fun idea in my head. Even when I’m providing a service that seems generous, I’m really doing it because it seemed like a fun system to build. If people like what I’ve made, that’s just a bonus.

This is related to yesterday’s post, “Travel without social praise”. Even despite what I’ve said here, I still have to ask myself if I’m doing something just for the praise.

Is this something I really want to do, or do I just like the image it represents?

If it feels like I’m doing it for the image, is that for my self-identity — how I see myself — the person I’d like to be for my own sake — or is it just being done for others?

One way I try to solve that question is by asking myself if I would do this thing if I was the last person on earth — or at very least, if I never told anyone about it.

( See also: “Announcing your plans makes you less motivated to accomplish them”. )

Sep 25, 2019
Travel without social praise

I met a couple who were thinking of quitting their jobs and travelling the world for a year. They asked my thoughts.

I suggested they should only do it if they don’t bring a camera, and don’t tell anyone but their family and few dear friends. No sharing on social media.

Why? Because we often live for others, without even realizing it. We are trying to impress an invisible crowd. We like the social reward of saying, “We’re travelling the world!” We imagine how friends and strangers would react to this big news.

We go places we think would be impressive to other people. We take photos that will make our life look wonderful when we share them. We want that praise — that social reward.

Do we really want to do this thing, for its own sake? Or do we just want the praise?

One way to find out is to see how appealing it would be to do it with no photos, and no sharing. Like the first person to run a marathon without talking about it.

If doing something makes us that kind of person, is it still true if we don’t announce it?

Sep 24, 2019
Travel without a phone

The first time, it was an accident.

I’d always wanted to go to Korea. I was so excited. I set out to explore and forgot my phone in the hotel.

I walked around Seoul for twelve hours that day and experienced so many wonderful things. I remember them all vividly now, years later, but I have no photos of it.

It was a relief to not document everything. I appreciated everything as a one-step process instead of a two-step process. I could just feel amazed, instead of feel amazed and hold up my camera to record it. Besides, how often do I look at those photos later, anyway? I find it more useful to refer to my journal of how I felt, instead of what I saw.

A few times, GPS could have helped, but because I didn’t have it, I had to go ask strangers for directions. Getting lost led me down some great little back roads I never would have found if I was following the map.

So now I intentionally travel without a phone.

I feel free and untethered. A break from connection.

Where you are is partially defined by where you are not. When you’re somewhere, you’re not somewhere else. But when you use your phone, you’re everywhere. You keep in touch with friends. You hear what’s going on at home. You see the screen exactly as you do anywhere else.

It’s wonderful to be cut off from everywhere else — to be more fully only there.

And it’s so nice to not know the time or where I am. Clocks and maps are useful inventions, but I see a moment better without them.

I appreciate a moment more when I know I’ll never see it again. I remember that day in Seoul better than I remember most photo-filled travels.

Sep 23, 2019

I’m starting a podcast today.

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Sep 22, 2019